Synthesis of Pumiliotoxine C from Molecular Nitrogen as a Nitrogen Source

Akashi, Masaya; Sato, Yoshihiro; Mori, Miwako

doi:10.1021/jo0104072

Cited by 35 publications

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“…[123] Most interestingly, however, is how many of these processes have found their way into more complicated syntheses. The syntheses of the natural products monomorine I, [124] ( AE )-lycopodine [121] and pumiliotoxine C [125] have all been developed from a dinitrogen feedstock. The broad chemistry accomplished by these systems is shown in Scheme 10.…”

Section: Reviewsmentioning

confidence: 99%

Activation of Molecular Nitrogen: Coordination, Cleavage and Functionalization of N₂ Mediated By Metal Complexes

2003

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Section: Reviewsmentioning

confidence: 99%

Activation of Molecular Nitrogen: Coordination, Cleavage and Functionalization of N₂ Mediated By Metal Complexes

2003

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“…All spectral data are in accordance with those reported in the literature. 21 To conclude; a short, catalytic asymmetric synthesis of (K)-pumiliotoxin C has been developed that is based on two tandem catalytic reactions. Starting with an asymmetric conjugate addition-allylic substitution reaction, two stereocenters are created in high yield with excellent enantioselectivity and high diastereoselectivity.…”

Section: Resultsmentioning

confidence: 99%

The asymmetric synthesis of (−)-pumiliotoxin C using tandem catalysis

et al. 2004

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“…Various 1,4-diketones (41) were treated with 32a prepared from TiCl 4 , Li, TMSCl and CsF under nitrogen in THF to give pyrrole derivatives (43) in good yields (Table 8). 25 These results indicated that titanium-nitrogen complex 32a could react with two keto-carbonyl groups intramolecularly to give pyrrole derivatives.…”

Section: N Hmentioning

confidence: 99%

Synthesis of Nitrogen Heterocycles Utilizing Molecular Nitrogen as a Nitrogen Source and Attempt to Use Air Instead of Nitrogen Gas

Mori¹

2009

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Nitrogen fixation using transition metals is a challenging subject. Using a titanium-nitrogen complex, discovered by Yamamoto in 1967, and titanium isocyanate complex, molecular nitrogen could be incorporated into organic compounds to afford various heterocyclic compounds. Furthermore, novel titanium-catalyzed nitrogenation procedure was developed. That is, a THF solution of TiCl 4 or Ti(O i Pr) 4 , and an excess amount of Li and TMSCl was stirred under nitrogen (1 atm) at room temperature overnight and to this solution was added phthalic anhydride. The whole solution was refluxed overnight to afford a phthalimide in over 100 % yield. Using the stoichiometric conditions of the novel nitrogenation, various indole, pyrrole, pyrrolizine, indolizine derivatives and lactams were obtained in good to moderate yields after usual workup. Although the structure of the titanium-nitrogen complex has not been determined yet, the complex is thought to be a mixture of N(TMS) 3 , TiX 2 N(TMS) 2 and XTi=NTMS. Nitrogen in air could be directly fixed using this method, and the natural products, such as monomoline I, lycopodine and pumiliotoxin C, could be synthesized from nitrogen in air as a nitrogen source. CONTENTS 1. Introduction 2. Synthesis of Nitrogen Heterocycles Using Titanium Isocyanate Complex and Palladium Complex

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Synthesis of Pumiliotoxine C from Molecular Nitrogen as a Nitrogen Source

Cited by 35 publications

References 12 publications

Activation of Molecular Nitrogen: Coordination, Cleavage and Functionalization of N₂ Mediated By Metal Complexes

Activation of Molecular Nitrogen: Coordination, Cleavage and Functionalization of N₂ Mediated By Metal Complexes

The asymmetric synthesis of (−)-pumiliotoxin C using tandem catalysis

Synthesis of Nitrogen Heterocycles Utilizing Molecular Nitrogen as a Nitrogen Source and Attempt to Use Air Instead of Nitrogen Gas

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Synthesis of Pumiliotoxine C from Molecular Nitrogen as a Nitrogen Source

Cited by 35 publications

References 12 publications

Activation of Molecular Nitrogen: Coordination, Cleavage and Functionalization of N2 Mediated By Metal Complexes

Activation of Molecular Nitrogen: Coordination, Cleavage and Functionalization of N2 Mediated By Metal Complexes

The asymmetric synthesis of (−)-pumiliotoxin C using tandem catalysis

Synthesis of Nitrogen Heterocycles Utilizing Molecular Nitrogen as a Nitrogen Source and Attempt to Use Air Instead of Nitrogen Gas

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Activation of Molecular Nitrogen: Coordination, Cleavage and Functionalization of N₂ Mediated By Metal Complexes

Activation of Molecular Nitrogen: Coordination, Cleavage and Functionalization of N₂ Mediated By Metal Complexes